The Caribbean All-Inclusive Resort Guide

It is that time of year for those of us in the norther latitudes when the leaves are dropping, days are shortening and temperatures are cooling. The idea of taking a break somewhere in the middle of the winter season has officially become appealing. However, rising costs have us digging deeper for bargains more than ever. One of the best ways to manage your dollar better is packaging your flight, hotel, transportation and even excursions. Better yet, it is time to brush off any preconceptions and visit an all-inclusive resort. You will forget about winter the moment you make your reservation!

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What is an All-Inclusive?

Caribbean Beach Resort

For those of you that have never heard of or have resisted an all-inclusive vacation, I cannot emphasize enough how much you are missing. There are so many aspects of an all-inclusive to mention but “relaxation “is first and foremost. There is simply no other way to summarize a beach vacation where your wallet remains locked in a safe for the entire trip. This doesn’t mean you are adding charges to your room that will require a defibrillator at check out. On the contrary, you’re not adding anything because as the name implies, all costs are included up front. This includes all meals, snacks, drinks (alcoholic and non-alcoholic), amenities (beach, pool, fitness center, etc.), housekeeping, entertainment and more. Additionally, most resorts offer multiple restaurant choices along with the standard buffet.

When selecting a resort, most destinations discussed here will have plenty of options. If it is your first all-inclusive vacation, you may want to stick with some of the larger chains such as Riu or Sandos. With these established hotels, you can feel more secure about the quality of amenities, food and guest experience. Typically, you can expect the same levels of service regardless of the country your visiting.


A primary misconception of all-inclusive resorts is the perceived lack of quality when it comes to the cuisine. While I agree that there are the occasional misses, the recent rise of food quality at these resorts has been remarkable. Picking the right resort can now mean having your fill of bacon at breakfast and sushi at dinner. Most resorts now have an international buffet where you can choose to have breakfast, lunch and dinner without reservation. It doesn’t get any more family friendly than allowing your kids to freely pick from wide selection of pastas, pizza, burgers, fires and more. For older visitors, salad bars, fish, cut meat stations, local fare and rotating ethnic (Chinese, barbecue) dishes are the norm.

The food options don’t stop there as most reasonably sized resorts (200 rooms or larger) will have additional dining options. These include popular Italian, Japanese and steakhouse options. Check out the amenity lists under each hotel to get a better sense of what they have to offer and if reservations are required. Additionally, there is usually a super-informal lunch area, typically found near the pool, where hot dogs, hamburgers and nachos are served. This allows you to keep the beach vibe going strong! If you miss a meal, don’t worry, snacks are available 24hrs at most resorts.

When it comes to any of these dining options, keep your expectations in check. Getting a quality steak is difficult anywhere and an all-inclusive resort is not the place to look for perfection. With that said, if you are there to relax and enjoy yourself, don’t let your inner food critic ruin your time.

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At an all-inclusive resort, your drinks, alcoholic and non-alcoholic, are included. Bars usually open around 11:30am and continue throughout the day with the pool bars closing around 5pm and lobby bars until after midnight. If your wanting top shelf liquors, book with a higher end resort as otherwise, native liquors will most often be served. This is hardly an issue when sipping a strawberry daquiri or pina colada. Keep in mind many of our favorites are actually from these regions such as Bacardi Rum and Kahlua.

Although mostly a misconception, weak drinks is only an issue if you are planning on getting hammered at 2 in the afternoon. While this is appealing to some, most people are looking to sip a drink for relaxation and not full-on party mode. Likewise, the staff is also keeping this in mind and trained to allow people to enjoy themselves without overindulging. If however, this is what you are looking for, I have never seen a bartender deny someone a double or straight up shot when requested. I once befriended a bartender who told me to waive at him with two fingers if I wanted a double. With that said, you may want to select a resort that caters more toward the spring-breaker and less family oriented as there is no shortage of either.


Hotel décor has been trending away from traditional flowery, tropical colors and designs in favor of more contemporary whites with vibrant accent colors like purples or bright greens. While I cannot say I am a huge fan of this, the overall feel is definitely more upscale and sophisticated. In your room, linens, curtains and towels will most likely be monotone with white walls, a desk, small couch and perhaps a chair or two. International television stations are offered but again, don’t set your expectations too high as the rooms are meant for comfort in the limited time your in it.

Most resorts provide a complimentary mini-bar that is stocked daily, while some also provide full bottle service of local liquors. Tubs are not common unless you upgrade your room or reserve a suite. I have never found hot water an issue as these facilities tend to have massive infrastructure to serve the hundreds of guest that stay at any given time. Water in the rooms is often non-drinkable so make use of the free bottled water in your fridge.

Being in the tropics and with the rooms often nestled in jungle environments, ants and other insects may make an appearance, especially on ground floors. After staying at a dozen different resorts, I have only seen this once and it was of little inconvenience. The staff immediately responded and the problem was resolved. With that said, the older the resort the more likely issues such as pests, low hot water and leaks may be an issue. I tend to ignore negative reviews about the condition of the rooms unless the age of them is a recurring comment.

Best All-Inclusive Destinations


The enormous benefit of a trip to Mexico is the proximity. A 5 hour flight can move your from Boston to the perpetual 80 degree temperatures of Cancun, Mexico. Based on its proximity, you should start your search here and include the areas south and north in what has become known as the Mayan Riviera. The expansive coastline of white sand beaches has impeccably clear, turquoise waters that any photographer can capture. There is no science to the destination, only amazement of the natural beauty our southern neighbor offers.

Cancun’s hotel zone is a unreal stretch of resorts that is unrivaled in the western hemisphere. One sole boulevard connects the entire length of what amounts to be one hotel after another. Mixed in between are several malls, retail plazas, night clubs, restaurants and convention centers. The strip is easily traversed with the inexpensive local buses that pass every few minutes.

Picking a hotel in Cancun is somewhat daunting simply due to it’s sheer size. With water on both sides of the thin strip of land, most rooms will have great views that will encourage you to actually use your balcony. It is important to research the hotel to see if it caters more to the spring-break crowd, adults-only or families.

While Cancun is quite urban, the area south known as the Mayan Riviera is loaded with new complexes of mostly low rise buildings that lie amidst tropical foliage. Play Del Carmen is about 1 hour south of Cancun International Airport and was one of the first areas developed outside of Cancun. It is now a hub of resorts that include all of the recognizable brands who cannot resist the draw of the perfect beaches found there. A newer area just north of Cancun known as Playa Mujeres, is quickly growing with large all inclusive resorts leading the way. Being brand new, you have the benefit of knowing the real estate is well maintained.

Mexico also has many historical sites within easy driving distance making it one of the only all-inclusive destinations where leaving your resort is tempting. Tulum, Chichen Itza and Xcaret are great adventures you should consider while Cozumel and Isla Mujeres offer views of Mexican island life.

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Dominican Republic

Similar to the north and south shores of Cancun, the beaches of Dominican Republic have seen explosive growth over the last few decades. Modern roads now lead from the international airports to the resort areas of Punta Cana, Puerta Plata and La Romana. Punta Cana has seemingly taken the lead with lush landscaped, low-rise resorts lining the coast. Although not as clear as the waters or white sanded as Mexico, the natural beauty and tropical weather making it a great destination.

Second to Mexico in hotel volume, you will find some influence of Dominican food and life at the resorts but with the case of most all-inclusive, it is more about the relaxation than the culture. Day trips are available throughout the island as are snorkeling and scuba trips.


While not as developed as the first two on this list, Jamaica offers the original island vibe with its’ reggae and jerk meat. There is an undeniable allure of the beats of reggae playing in the background as you chill on the beach amongst palm trees. You will undoubtedly return home with a passion for Bob Marley and renewed vigor to maintain relaxation in life!

Jamaica also offers a very distinct culinary specialty with its jerk seasoning. Most usually on chicken or pork, jerk meat is a spicy blend that includes the incredibly hot scotch bonnet pepper. Curiously, a slice of wonder bread is usually included on the side. If you are fortunate, your resort will offer up this delicacy. If not you won’t have to venture far off campus to find some. Ask your hotels front desk for suggestions.

Also found on this tropical island are the Blue Mountains where coffee lovers can taste freshly picked coffee beans and rum lovers can visit the Appleton Estate. Montego Bay, Negril and Ocho Rios are the 3 primary resort destinations that are all relatively easy to reach due to the compactness of the island and despite major highways being somewhat limited.

When to Visit

With weather that is quite consistent in the 80’s to low 90’s, the Caribbean offers a fantastic opportunity to escape the cold of the winter. However, if you want to save money, traveling to tropical destinations is great all year. Keep in mind that June-August are the warmest and September-October are the peak of Hurricane season. If you avoid the busy school vacation dates, you can easily save 10-20% on your trip. No matter what the time of year, the sun will be far more potent as it remains high in the sky. Bring your sunscreen and don’t forget to reapply consistently.

Looking for more travel ideas? Read Your Guide to Universal Orlando: Islands of Adventure and Universal Studios and An Insightful Travel Guide to Thailand!

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